Maybe I'm missing something in your comment here, but - Python and Ruby already have smooth dev server installs. In fact, much smoother than PHP, as you don't need apache or fancy permissions to just run something local.
Start as J. Random Noob: they need to install python, virtualenv, etc. before learning how to create a module, create multiple config files and so forth.
Technically PHP isn't much easier if you need to compile it, configure Apache, etc. but in practice they just pay $1/mo for a crappy hosted account where they simply upload a file and start fiddling.
This is a trivial distinction for a professional developer but there are quite a few PHP users who started with a personal homepage and grew from there – and despite the stereotype, they're not all designers, either. That's why I like the Rails.app idea: give today's bright 13-year-old a nice, easy path to getting something visible and let them get hooked before they need to learn all of this other stuff.
Ruby, rails: "rails server" Ruby, sinatra: "ruby <sinatra script>" Python, django: "python manage.py runserver"
All of these spin up an app server on some port > 1024. I'm honestly not sure how it can get much easier than that.